Organic molecules for use in optoelectronic devices

ABSTRACT

An organic molecule is disclosed having a structure of formula I, 
     
       
         
         
             
             
         
       
         
         
           
             wherein 
             T is selected from the group consisting of CN and CF 3 ; 
             V, W and Y is independently from each other selected from the group consisting of CN, CF 3  and R 2 ; 
             Z is at each occurrence independently from another selected from the group consisting of a direct bond, CR 3 R 4 , C═CR 3 R 4 , C═O, C═NR 3 , NR 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 ; 
             wherein 
             exactly one substituent selected from the group consisting of T, V, W and Y is CN; and 
             exactly one substituent selected from the group consisting of T, V, W and Y is CF 3 .

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to German Patent Application No. 102018 107 166.3, filed Mar. 26, 2018, the disclosure of which isincorporated by reference herein in its entireties.

FIELD OF INVENTION

The invention relates to organic molecules and their use in organiclight-emitting diodes (OLEDs) and in other optoelectronic devices.

BRIEF DESCRIPTION OF THE DRAWINGS

Exemplary embodiments of the present invention will be described belowin more detail, with reference to the accompanying drawings, of which:

FIG. 1 is an emission spectrum of Example 1 (10% by weight) in PMMA.

FIG. 2 is an emission spectrum of Example 2 (10% by weight) in PMMA.

DETAILED DESCRIPTION OF EXEMPLARY EMBODIMENTS OF THE INVENTION

Exemplary embodiments of the invention will now be discussed in furtherdetail. This invention may, however, be embodied in many different formsand should not be construed as limited to the embodiments set forthherein.

The object of the present invention is to provide molecules which aresuitable for use in organic optoelectronic devices.

This object is achieved by the invention which provides a new class oforganic molecules.

According to the invention the organic molecules are purely organicmolecules, i.e. they do not contain any metal ions in contrast to metalcomplexes known for use in organic optoelectronic devices.

According to the present invention, the organic molecules exhibitemission maxima in the blue, sky-blue or green spectral range. Theorganic molecules exhibit in particular emission maxima between 420 nmand 520 nm, preferably between 440 nm and 495 nm, more preferablybetween 450 nm and 470 nm. The photoluminescence quantum yields of theorganic molecules according to the invention are, in particular, 20% ormore. The molecules according to the invention exhibit in particularthermally activated delayed fluorescence (TADF). The use of themolecules according to the invention in an optoelectronic device, forexample an organic light-emitting diode (OLED), leads to higherefficiencies of the device. Corresponding OLEDs have a higher stabilitythan OLEDs with known emitter materials and comparable color.

The organic light-emitting molecules of the invention comprise orconsist of a structure of Formula I,

T is selected from the group consisting of CN and CF₃.

V, W and Y is independently from each other selected from the groupconsisting of CN, CF₃ and R².

Z is at each occurrence independently from another selected from thegroup consisting of a direct bond, CR³R⁴, C═CR³R⁴, C═O, C═NR³, NR³, O,SiR³R⁴, S, S(O) and S(O)₂.

R¹ is at each occurrence independently from another selected from thegroup consisting of hydrogen,

deuterium,

-   C₁-C₅-alkyl,    -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;-   C₂-C₈-alkenyl,    -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;-   C₂-C₈-alkynyl,    -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and-   C₆-C₁₈-aryl,    -   which is optionally substituted with one or more substituents        independently from each other selected from the group consisting        of Me, ^(i)Pr, ^(t)Bu and Ph.

R² is at each occurrence independently from another selected from thegroup consisting of hydrogen, deuterium,

-   C₁-C₅-alkyl,    -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;-   C₂-C₈-alkenyl,    -   wherein one or more hydrogen atoms are optionally substituted by        deuterium;-   C₂-C₈-alkynyl,    -   wherein one or more hydrogen atoms are optionally substituted by        deuterium; and-   C₆-C₁₈-aryl,    -   which is optionally substituted with one or more substituents        independently from each other selected from the group consisting        of Me, ^(i)Pr, ^(t)Bu and Ph.

R^(a), R³ and R⁴ is at each occurrence independently from anotherselected from the group consisting of hydrogen, deuterium, N(R⁵)₂, OR⁵,Si(R⁵)₃, B(OR⁵)₂, OSO₂R⁵, CF₃, CN, F, Br, I,

-   C₁-C₄₀-alkyl,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₁-C₄₀-alkoxy,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₁-C₄₀-thioalkoxy,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₂-C₄₀-alkenyl,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₂-C₄₀-alkynyl,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₆-C₆₀-aryl,    -   which is optionally substituted with one or more substituents        R⁵; and-   C₃-C₅₇-heteroaryl,    -   which is optionally substituted with one or more substituents        R⁵.

R⁵ is at each occurrence independently from another selected from thegroup consisting of hydrogen, deuterium, N(R⁶)₂, OR⁶, Si(R⁶)₃, B(OR⁶)₂,OSO₂R⁶, CF₃, CN, F, Br, I,

-   C₁-C₄₀-alkyl,    -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;-   C₁-C₄₀-alkoxy,    -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;-   C₁-C₄₀-thioalkoxy,    -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;-   C₂-C₄₀-alkenyl,    -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;-   C₂-C₄₀-alkynyl,    -   which is optionally substituted with one or more substituents R⁶        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,        C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;-   C₆-C₆₀-aryl,    -   which is optionally substituted with one or more substituents        R⁶; and-   C₃-C₅₇-heteroaryl,    -   which is optionally substituted with one or more substituents        R⁶.

R⁶ is at each occurrence independently from another selected from thegroup consisting of hydrogen, deuterium, OPh, CF₃, CN, F,

-   C₁-C₅-alkyl,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₁-C₅-alkoxy,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₁-C₅-thioalkoxy,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₂-C₅-alkenyl,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₂-C₅-alkynyl,    -   wherein optionally one or more hydrogen atoms are independently        from each other substituted by deuterium, CN, CF₃, or F;-   C₆-C₁₈-aryl,    -   which is optionally substituted with one or more C≡C-alkyl        substituents;-   C₃-C₁₇-heteroaryl,    -   which is optionally substituted with one or more C≡C-alkyl        substituents;

N(C₆-C₁₈-aryl)₂,

N(C₃-C₁₇-heteroaryl)₂; and

N(C₃-C₁₇-heteroaryl)(C₆-C₁₈-aryl).

According to the invention, exactly one (one and only one) substituentselected from the group consisting of T, V, W and Y is CN;

and exactly one substituent selected from the group consisting of T, V,W and Y is CF₃.

In a further embodiment of the invention, the organic molecule comprisesor consists of a structure of Formula Ia:

wherein

W^(#) is selected from the group consisting of CN and CF₃,

wherein exactly one substituent selected from the group consisting of Tand W is CN;

and exactly one (i.e. the other) substituent selected from the groupconsisting of T and W is CF₃; and wherein the aforementioned definitionsapply.

In a further embodiment of the invention, the organic molecule comprisesor consists of a structure of Formula IIa:

wherein

W^(#) is selected from the group consisting of CN and CF₃,

wherein exactly one substituent selected from the group consisting of Tand W^(#) is CN; and exactly one (i.e. the other) substituent selectedfrom the group consisting of T and W^(#) is CF₃; and wherein theaforementioned definitions apply.

In one embodiment, R¹ and R² is at each occurrence independently fromanother selected from the group consisting of hydrogen (H), methyl,mesityl, tolyl and phenyl. The term tolyl comprises 2-tolyl, 3-tolyl and4-tolyl.

In one embodiment, R¹ and R² is at each occurrence independently fromanother selected from the group consisting of hydrogen (H), methyl, andphenyl.

In one embodiment, R¹ and R² is hydrogen (H).

In one embodiment, T is CN and V is CF₃.

In one embodiment, T is CN and W is CF₃.

In one embodiment, T is CN and Y is CF₃.

In one embodiment, T is CF₃ and V is CN.

In one embodiment, T is CF₃ and W is CN.

In one embodiment, T is CF₃ and Y is CN.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of H,

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,

and N(Ph)₂.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of H,

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph.

In a further embodiment of the invention, R^(a) is at each occurrenceindependently from another selected from the group consisting of H,

-   Me,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, and Ph.

In a further embodiment of the invention, R^(a) is H at each occurrence

In a further embodiment of the invention, the organic molecule comprisesor consists of a structure selected from the group of Formula lib,Formula IIb-2, Formula IIb-3 or Formula IIb-4:

wherein

-   R^(b) is at each occurrence independently from another selected from    the group consisting of deuterium,-   N(R⁵)₂,-   OR⁵,-   Si(R⁵)₃,-   B(OR⁵)₂,-   OSO₂R⁵,-   CF₃,-   CN,-   F,-   Br,-   I,-   C₁-C₄₀-alkyl,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₁-C₄₀-alkoxy,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₁-C₄₀-thioalkoxy,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₂-C₄₀-alkenyl,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₂-C₄₀-alkynyl,    -   which is optionally substituted with one or more substituents R⁵        and    -   wherein one or more non-adjacent CH₂-groups are optionally        substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,        C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;-   C₆-C₆₀-aryl,    -   which is optionally substituted with one or more substituents        R⁵; and-   C₃-C₅₇-heteroaryl,    -   which is optionally substituted with one or more substituents        R⁵.

Apart from that the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecule comprisesor consists of a structure selected from the group of Formula IIc,Formula IIc-2, Formula IIc-3 or Formula IIc-4:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,

and N(Ph)₂.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   CN,-   CF₃,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph, and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph.

In a further embodiment of the invention, R^(b) is at each occurrenceindependently from another selected from the group consisting of

-   Me,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, ON, CF₃, and Ph.

In the following, exemplary embodiments of the organic molecule of theinvention are shown:

wherein for W, V, Y, R¹, R², R^(a), R³, R⁴ and R⁵ the aforementioneddefinitions apply.

In one embodiment, R^(a) and R⁵ is at each occurrence independently fromanother selected from the group consisting of hydrogen (H), methyl (Me),i-propyl (CH(CH₃)₂) (^(i)Pr), t-butyl (^(t)Bu), phenyl (Ph), CN, CF₃,and diphenylamine (NPh₂).

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula III:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IIIa:

wherein

-   R^(C) is at each occurrence independently from another selected from    the group consisting of-   Me,-   ^(i)Pr,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃, and Ph,-   pyridinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, CN, CF₃, and Ph,-   pyrimidinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, CN, CF₃, and Ph,-   carbazolyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, CN, CF₃, and Ph,-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, Pr, ^(t)Bu, CN, CF₃, and Ph,

and N(Ph)₂.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IIIb:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IIIIc:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IIId:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula IV:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IVa:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IVb:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IVc:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula IVd:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula V:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula Va:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula Vb:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula Vc:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula Vd:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula VI:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIa:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIb:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIc:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VId:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula VII:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIIa:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIIb:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIIc:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIId:

wherein the aforementioned definitions apply.

In one embodiment of the invention, the organic molecules comprise orconsist of a structure of Formula VIII:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula Villa:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIIb:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIIIc:

wherein the aforementioned definitions apply.

In a further embodiment of the invention, the organic molecules compriseor consist of a structure selected from the group of Formula VIId:

wherein the aforementioned definitions apply.

In one embodiment of the invention R^(c) is at each occurrenceindependently from another selected from the group consisting of

-   Me,-   ^(i)Pr,-   ^(t)Bu,-   Ph, which is optionally substituted with one or more substituents    independently from each other selected from the group consisting of    Me, ^(i)Pr, ^(t)Bu, ON, CF₃ and Ph; and-   triazinyl, which is optionally substituted with one or more    substituents independently from each other selected from the group    consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph.

As used throughout the present application, the terms “aryl” and“aromatic” may be understood in the broadest sense as any mono-, bi- orpolycyclic aromatic moieties. Accordingly, an aryl group contains 6 to60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromaticring atoms, of which at least one is a heteroatom. Notwithstanding,throughout the application the number of aromatic ring atoms may begiven as subscripted number in the definition of certain substituents.In particular, the heteroaromatic ring includes one to threeheteroatoms. Again, the terms “heteroaryl” and “heteroaromatic” may beunderstood in the broadest sense as any mono-, bi- or polycyclichetero-aromatic moieties that include at least one heteroatom. Theheteroatoms may at each occurrence be the same or different and beindividually selected from the group consisting of N, O and S.Accordingly, the term “arylene” refers to a divalent substituent thatbears two binding sites to other molecular structures and therebyserving as a linker structure. In case, a group in the exemplaryembodiments is defined differently from the definitions given here, forexample, the number of aromatic ring atoms or number of heteroatomsdiffers from the given definition, the definition in the exemplaryembodiments is to be applied. According to the invention, a condensed(annulated) aromatic or heteroaromatic polycycle is built of two or moresingle aromatic or heteroaromatic cycles, which formed the polycycle viaa condensation reaction.

In particular, as used throughout the present application the term arylgroup or heteroaryl group comprises groups which can be bound via anyposition of the aromatic or heteroaromatic group, derived from benzene,naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene,perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene,pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran,thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole,indole, isoindole, carbazole, pyridine, quinoline, isoquinoline,acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline,benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole,imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole,pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole,benzoxazole, napthooxazole, anthroxazol, phenanthroxazol, isoxazole,1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine,pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine,phenazine, naphthyridine, carboline, benzocarboline, phenanthroline,1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole,1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine,pteridine, indolizine and benzothiadiazole or combinations of theabovementioned groups.

As used throughout the present application the term cyclic group may beunderstood in the broadest sense as any mono-, bi- or polycyclicmoieties.

As used throughout the present application the term biphenyl as asubstituent may be understood in the broadest sense as ortho-biphenyl,meta-biphenyl, or para-biphenyl, wherein ortho, meta and para is definedin regard to the binding site to another chemical moiety.

As used throughout the present application the term alkyl group may beunderstood in the broadest sense as any linear, branched, or cyclicalkyl substituent. In particular, the term alkyl comprises thesubstituents methyl (Me), ethyl (Et), n-propyl (^(n)Pr), i-propyl(^(i)Pr), cyclopropyl, n-butyl (^(n)Bu), i-butyl (^(i)Bu), s-butyl(^(s)Bu), t-butyl (^(t)Bu), cyclobutyl, 2-methylbutyl, n-pentyl,s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl,t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl,2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl,1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl,1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]-octyl, 2-(2,6-dimethyl)octyl,3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluorethyl,1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl,1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl,1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl,1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl,1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl,1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl,1,1-diethyl-n-tetradec-1-yl, 1,1-diethyln-n-hexadec-1-yl,1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl,1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl,1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

As used throughout the present application the term alkenyl compriseslinear, branched, and cyclic alkenyl substituents. The term alkenylgroup exemplarily comprises the substituents ethenyl, propenyl, butenyl,pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl,octenyl, cyclooctenyl or cyclooctadienyl.

As used throughout the present application the term alkynyl compriseslinear, branched, and cyclic alkynyl substituents. The term alkynylgroup exemplarily comprises ethynyl, propynyl, butynyl, pentynyl,hexynyl, heptynyl or octynyl.

As used throughout the present application the term alkoxy compriseslinear, branched, and cyclic alkoxy substituents. The term alkoxy groupexemplarily comprises methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

As used throughout the present application the term thioalkoxy compriseslinear, branched, and cyclic thioalkoxy substituents, in which the O ofthe exemplarily alkoxy groups is replaced by S.

As used throughout the present application, the terms “halogen” and“halo” may be understood in the broadest sense as being preferablyfluorine, chlorine, bromine or iodine.

Whenever hydrogen (H) is mentioned herein, it could also be replaced bydeuterium at each occurrence.

It is understood that when a molecular fragment is described as being asubstituent or otherwise attached to another moiety, its name may bewritten as if it were a fragment (e.g. naphtyl, dibenzofuryl) or as ifit were the whole molecule (e.g. naphthalene, dibenzofuran). As usedherein, these different ways of designating a substituent or attachedfragment are considered to be equivalent.

In one embodiment, the organic molecules according to the invention havean excited state lifetime of not more than 150 μs, of not more than 100μs, in particular of not more than 50 μs, more preferably of not morethan 10 μs or not more than 7 μs in a film of poly(methyl methacrylate)(PMMA) with 10% by weight of organic molecule at room temperature.

In one embodiment of the invention, the organic molecules according tothe invention represent thermally-activated delayed fluorescence (TADF)emitters, which exhibit a ΔEs_(T) value, which corresponds to the energydifference between the first excited singlet state (S1) and the firstexcited triplet state (T1), of less than 5000 cm⁻¹, preferably less than3000 cm⁻¹, more preferably less than 1500 cm⁻¹, even more preferablyless than 1000 cm⁻¹ or even less than 500 cm⁻¹.

In a further embodiment of the invention, the organic moleculesaccording to the invention have an emission peak in the visible ornearest ultraviolet range, i.e., in the range of a wavelength of from380 to 800 nm, with a full width at half maximum of less than 0.50 eV,preferably less than 0.48 eV, more preferably less than 0.45 eV, evenmore preferably less than 0.43 eV or even less than 0.40 eV in a film ofpoly(methyl methacrylate) (PMMA) with 10% by weight of organic moleculeat room temperature.

In a further embodiment of the invention, the organic moleculesaccording to the invention have a “blue material index” (BMI),calculated by dividing the photoluminescence quantum yield (PLQY) in %by the CIEy color coordinate of the emitted light, of more than 150, inparticular more than 200, preferably more than 250, more preferably ofmore than 300 or even more than 500.

Orbital and excited state energies can be determined either by means ofexperimental methods or by calculations employing quantum-chemicalmethods, in particular density functional theory calculations. Theenergy of the highest occupied molecular orbital E^(HOMO) is determinedby methods known to the person skilled in the art from cyclicvoltammetry measurements with an accuracy of 0.1 eV. The energy of thelowest unoccupied molecular orbital E^(LUMO) is determined as the onsetof the absorption spectrum.

The onset of an absorption spectrum is determined by computing theintersection of the tangent to the absorption spectrum with the x-axis.The tangent to the absorption spectrum is set at the low-energy side ofthe absorption band and at the point at half maximum of the maximumintensity of the absorption spectrum.

The energy of the first excited triplet state T1 is determined from theonset of the emission spectrum at low temperature, typically at 77 K.For host compounds, where the first excited singlet state and the lowesttriplet state are energetically separated by >0.4 eV, thephosphorescence is usually visible in a steady-state spectrum in2-Me-THF. The triplet energy can thus be determined as the onset of thephosphorescence spectrum. For TADF emitter molecules, the energy of thefirst excited triplet state T1 is determined from the onset of thedelayed emission spectrum at 77 K, if not otherwise stated measured in afilm of PMMA with 10% by weight of emitter. Both for host and emittercompounds, the energy of the first excited singlet state S1 isdetermined from the onset of the emission spectrum, if not otherwisestated measured in a film of PMMA with 10% by weight of host or emittercompound.

The onset of an emission spectrum is determined by computing theintersection of the tangent to the emission spectrum with the x-axis.The tangent to the emission spectrum is set at the high-energy side ofthe emission band and at the point at half maximum of the maximumintensity of the emission spectrum.

A further aspect of the invention relates to a process for preparingorganic molecules (with an optional subsequent reaction) according tothe invention, wherein a R²-substituted,cyano/trifluoromethyl-substituted 1-bromo-2-fluorophenyl is used as areactant:

According to the invention, in the reaction for the synthesis of E1 aboronic acid or an equivalent boronic acid ester can be used instead ofa boronic pinacol ester.

Typically, Pd₂(dba)₃ (tris(dibenzylideneacetone)dipalladium(0)) is usedas a Pd catalyst, but alternatives are known in the art. For example,the ligand may be selected from the group consisting of S-Phos([2-dicyclohexylphoshino-2′,6′-dimethoxy-1,1′-biphenyl]; or SPhos),X-Phos (2-(dicyclohexylphosphino)-2″,4″, 6″-triisopropylbiphenyl; orXPhos), and P(Cy)₃ (tricyclohexylphosphine). The salt is, for example,selected from tribasic potassium phosphate and potassium acetate and thesolvent can be a pure solvent, such as toluene or dioxane, or a mixture,such as toluene/dioxane/water or dioxane/toluene. A person of skill inthe art can determine which Pd catalyst, ligand, salt and solventcombination will result in high reaction yields.

For the reaction of a nitrogen heterocycle in a nucleophilic aromaticsubstitution with an aryl halide, preferably an aryl fluoride, typicalconditions include the use of a base, such as tribasic potassiumphosphate or sodium hydride, for example, in an aprotic polar solvent,such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF), forexample.

An alternative synthesis route comprises the introduction of a nitrogenheterocycle via copper- or palladium-catalyzed coupling to an arylhalide or aryl pseudohalide, preferably an aryl bromide, an aryl iodide,aryl triflate or an aryl tosylate.

A further aspect of the invention relates to the use of an organicmolecule according to the invention as a luminescent emitter or as anabsorber, and/or as host material and/or as electron transport material,and/or as hole injection material, and/or as hole blocking material inan organic optoelectronic device.

The organic electroluminescent device may be understood in the broadestsense as any device based on organic materials that is suitable foremitting light in the visible or nearest ultraviolet (UV) range, i.e.,in the range of a wavelength of from 380 to 800 nm. More preferably,organic electroluminescent device may be able to emit light in thevisible range, i.e., of from 400 to 800 nm.

In the context of such use, the optoelectronic device is moreparticularly selected from the group consisting of:

-   -   organic light-emitting diodes (OLEDs),    -   light-emitting electrochemical cells,    -   OLED sensors, especially in gas and vapour sensors not        hermetically externally shielded,    -   organic diodes,    -   organic solar cells,    -   organic transistors,    -   organic field-effect transistors,    -   organic lasers and    -   down-conversion elements.

In a preferred embodiment in the context of such use, the organicelectroluminescent device is a device selected from the group consistingof an organic light emitting diode (OLED), a light emittingelectrochemical cell (LEC), and a light-emitting transistor.

In the case of the use, the fraction of the organic molecule accordingto the invention in the emission layer in an organic optoelectronicdevice, more particularly in OLEDs, is 1% to 99% by weight, moreparticularly 5% to 80% by weight. In an alternative embodiment, theproportion of the organic molecule in the emission layer is 100% byweight.

In one embodiment, the light-emitting layer comprises not only theorganic molecules according to the invention but also a host materialwhose triplet (T1) and singlet (S1) energy levels are energeticallyhigher than the triplet (T1) and singlet (S1) energy levels of theorganic molecule.

A further aspect of the invention relates to a composition comprising orconsisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

In one embodiment, the light-emitting layer comprises (or (essentially)consists of) a composition comprising or consisting of:

-   (a) at least one organic molecule according to the invention, in    particular in the form of an emitter and/or a host, and-   (b) one or more emitter and/or host materials, which differ from the    organic molecule according to the invention and-   (c) optional one or more dyes and/or one or more solvents.

Particularly preferably the light-emitting layer EML comprises (or(essentially) consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one or more organic molecules according to the    invention E;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of at least one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

Preferably, energy can be transferred from the host compound H to theone or more organic molecules according to the invention E, inparticular transferred from the first excited triplet state T1(H) of thehost compound H to the first excited triplet state T1(E) of the one ormore organic molecules according to the invention E and/or from thefirst excited singlet state S1(H) of the host compound H to the firstexcited singlet state S1(E) of the one or more organic moleculesaccording to the invention E.

In a further embodiment, the light-emitting layer EML comprises (or(essentially) consists of) a composition comprising or consisting of:

-   (i) 1-50% by weight, preferably 5-40% by weight, in particular    10-30% by weight, of one organic molecule according to the invention    E;-   (ii) 5-99% by weight, preferably 30-94.9% by weight, in particular    40-89% by weight, of one host compound H; and-   (iii) optionally 0-94% by weight, preferably 0.1-65% by weight, in    particular 1-50% by weight, of at least one further host compound D    with a structure differing from the structure of the molecules    according to the invention; and-   (iv) optionally 0-94% by weight, preferably 0-65% by weight, in    particular 0-50% by weight, of a solvent; and-   (v) optionally 0-30% by weight, in particular 0-20% by weight,    preferably 0-5% by weight, of at least one further emitter molecule    F with a structure differing from the structure of the molecules    according to the invention.

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) in the range of from −5 to−6.5 eV and the at least one further host compound D has a highestoccupied molecular orbital HOMO(D) having an energy E^(HOMO)(D), whereinE^(HOMO)(H)>E^(HOMO)(D).

In a further embodiment, the host compound H has a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H) and the at leastone further host compound D has a lowest unoccupied molecular orbitalLUMO(D) having an energy E^(LUMO)(D), wherein E^(LUMO)(H)>E^(LUMO)(D).

In one embodiment, the host compound H has a highest occupied molecularorbital HOMO(H) having an energy E^(HOMO)(H) and a lowest unoccupiedmolecular orbital LUMO(H) having an energy E^(LUMO)(H), and

-   -   the at least one further host compound D has a highest occupied        molecular orbital HOMO(D) having an energy E^(HOMO)(D) and a        lowest unoccupied molecular orbital LUMO(D) having an energy        E^(LUMO)(D),    -   the organic molecule according to the invention E has a highest        occupied molecular orbital HOMO(E) having an energy E^(HOMO)(E)        and a lowest unoccupied molecular orbital LUMO(E) having an        energy E^(LUMO)(E),

wherein

E^(HOMO)(H)>E^(HOMO)(D) and the difference between the energy level ofthe highest occupied molecular orbital HOMO(E) of the organic moleculeaccording to the invention E (E^(HOMO)(E)) and the energy level of thehighest occupied molecular orbital HOMO(H) of the host compound H(E^(HOMO)(H)) is between −0.5 eV and 0.5 eV, more preferably between−0.3 eV and 0.3 eV, even more preferably between −0.2 eV and 0.2 eV oreven between −0.1 eV and 0.1 eV; and E^(LUMO)(H)>E^(LUMO)(D) and thedifference between the energy level of the lowest unoccupied molecularorbital LUMO(E) of the organic molecule according to the invention E(E^(LUMO)(E)) and the lowest unoccupied molecular orbital LUMO(D) of theat least one further host compound D (E^(LUMO)(D)) is between −0.5 eVand 0.5 eV, more preferably between −0.3 eV and 0.3 eV, even morepreferably between −0.2 eV and 0.2 eV or even between −0.1 eV and 0.1eV.

In a further aspect, the invention relates to an optoelectronic devicecomprising an organic molecule or a composition of the type describedhere, more particularly in the form of a device selected from the groupconsisting of organic light-emitting diode (OLED), light-emittingelectrochemical cell, OLED sensor, more particularly gas and vapoursensors not hermetically externally shielded, organic diode, organicsolar cell, organic transistor, organic field-effect transistor, organiclaser and down-conversion element.

In a preferred embodiment, the organic electroluminescent device is adevice selected from the group consisting of an organic light emittingdiode (OLED), a light emitting electrochemical cell (LEC), and alight-emitting transistor.

In one embodiment of the optoelectronic device of the invention, theorganic molecule according to the invention E is used as emissionmaterial in a light-emitting layer EML.

In one embodiment of the optoelectronic device of the invention thelight-emitting layer EML consists of the composition according to theinvention described here.

Exemplarily, when the organic electroluminescent device is an OLED, itmay exhibit the following layer structure:

1. substrate

2. anode layer A

3. hole injection layer, HIL

4. hole transport layer, HTL

5. electron blocking layer, EBL

6. emitting layer, EML

7. hole blocking layer, HBL

8. electron transport layer, ETL

9. electron injection layer, EIL

10. cathode layer,

wherein the OLED comprises each layer only optionally, different layersmay be merged and the OLED may comprise more than one layer of eachlayer type defined above.

Furthermore, the organic electroluminescent device may optionallycomprise one or more protective layers protecting the device fromdamaging exposure to harmful species in the environment including,exemplarily moisture, vapor and/or gases.

In one embodiment of the invention, the organic electroluminescentdevice is an OLED, which exhibits the following inverted layerstructure:

1. substrate

2. cathode layer

3. electron injection layer, EIL

4. electron transport layer, ETL

5. hole blocking layer, HBL

6. emitting layer, B

7. electron blocking layer, EBL

8. hole transport layer, HTL

9. hole injection layer, HIL

10. anode layer A

Wherein the OLED with an inverted layer structure comprises each layeronly optionally, different layers may be merged and the OLED maycomprise more than one layer of each layer types defined above.

In one embodiment of the invention, the organic electroluminescentdevice is an OLED, which may exhibit stacked architecture. In thisarchitecture, contrary to the typical arrangement, where the OLEDs areplaced side by side, the individual units are stacked on top of eachother. Blended light may be generated with OLEDs exhibiting a stackedarchitecture, in particular white light may be generated by stackingblue, green and red OLEDs. Furthermore, the OLED exhibiting a stackedarchitecture may optionally comprise a charge generation layer (CGL),which is typically located between two OLED subunits and typicallyconsists of a n-doped and p-doped layer with the n-doped layer of oneCGL being typically located closer to the anode layer.

In one embodiment of the invention, the organic electroluminescentdevice is an OLED, which comprises two or more emission layers betweenanode and cathode. In particular, this so-called tandem OLED comprisesthree emission layers, wherein one emission layer emits red light, oneemission layer emits green light and one emission layer emits bluelight, and optionally may comprise further layers such as chargegeneration layers, blocking or transporting layers between theindividual emission layers. In a further embodiment, the emission layersare adjacently stacked. In a further embodiment, the tandem OLEDcomprises a charge generation layer between each two emission layers. Inaddition, adjacent emission layers or emission layers separated by acharge generation layer may be merged.

The substrate may be formed by any material or composition of materials.Most frequently, glass slides are used as substrates. Alternatively,thin metal layers (e.g., copper, gold, silver or aluminum films) orplastic films or slides may be used. This may allow a higher degree offlexibility. The anode layer A is mostly composed of materials allowingto obtain an (essentially) transparent film. As at least one of bothelectrodes should be (essentially) transparent in order to allow lightemission from the OLED, either the anode layer A or the cathode layer Cis transparent.

Preferably, the anode layer A comprises a large content or even consistsof transparent conductive oxides (TCOs). Such anode layer A mayexemplarily comprise indium tin oxide, aluminum zinc oxide, fluorinedoped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide,molybdenum oxide, vanadium oxide, wolfram oxide, graphite, doped Si,doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or dopedpolythiophene.

Particularly preferably, the anode layer A (essentially) consists ofindium tin oxide (ITO) (e.g., (InO₃)0.9(SnO₂)0.1). The roughness of theanode layer A caused by the transparent conductive oxides (TCOs) may becompensated by using a hole injection layer (HIL). Further, the HIL mayfacilitate the injection of quasi charge carriers (i.e., holes) in thatthe transport of the quasi charge carriers from the TCO to the holetransport layer (HTL) is facilitated. The hole injection layer (HIL) maycomprise poly-3,4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate(PSS), MoO₂, V₂O₅, CuPC or CuI, in particular a mixture of PEDOT andPSS. The hole injection layer (HIL) may also prevent the diffusion ofmetals from the anode layer A into the hole transport layer (HTL). TheHIL may exemplarily comprise PEDOT:PSS (poly-3,4-ethylendioxy thiophene:polystyrene sulfonate), PEDOT (poly-3,4-ethylendioxy thiophene), mMTDATA(4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD(2,2′,7,7′-tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene), DNTPD(N1,N1′-(biphenyl-4,4′-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine),NPB(N,N′-nis-(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine),NPNPB (N,N′-diphenyl-N,N′-di-[4-(N, N-diphenyl-amino)phenyl]benzidine),MeO-TPD (N,N,N′,N′-tetrakis(4-methoxyphenyl)benzidine), HAT-CN(1,4,5,8,9,11-hexaazatriphenylen-hexacarbonitrile) and/or Spiro-NPD(N,N′-diphenyl-N,N′-bis-(1-naphthyl)-9,9′-spirobifluorene-2,7-diamine).

Adjacent to the anode layer A or hole injection layer (HIL) typically ahole transport layer (HTL) is located. Herein, any hole transportcompound may be used. Exemplarily, electron-rich heteroaromaticcompounds such as triarylamines and/or carbazoles may be used as holetransport compound. The HTL may decrease the energy barrier between theanode layer A and the light-emitting layer EML. The hole transport layer(HTL) may also be an electron blocking layer (EBL). Preferably, holetransport compounds bear comparably high energy levels of their tripletstates T1. Exemplarily the hole transport layer (HTL) may comprise astar-shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine(TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [alpha]-NPD(poly(4-butylphenyl-diphenyl-amine)), TAPC(4,4′-cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA(4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD,NPB, NPNPB, MeO-TPD, HAT-CN and/or TrisPcz(9,9′-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9′H-3,3′-bicarbazole).In addition, the HTL may comprise a p-doped layer, which may be composedof an inorganic or organic dopant in an organic hole-transportingmatrix. Transition metal oxides such as vanadium oxide, molybdenum oxideor tungsten oxide may exemplarily be used as inorganic dopant.Tetrafluorotetracyanoquinodimethane (F₄-TCNQ),copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes mayexemplarily be used as organic dopant.

The EBL may exemplarily comprise mCP (1,3-bis(carbazol-9-yl)benzene),TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl) biphenyl), tris-Pcz, CzSi(9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and/orDCB (N,N′-dicarbazolyl-1,4-dimethyl benzene).

Adjacent to the hole transport layer (HTL), typically, thelight-emitting layer EML is located. The light-emitting layer EMLcomprises at least one light emitting molecule. Particularly, the EMLcomprises at least one light emitting molecule according to theinvention E. In one embodiment, the light-emitting layer comprises onlythe organic molecules according to the invention E. Typically, the EMLadditionally comprises one or more host materials H. Exemplarily, thehost material H is selected from CBP (4,4′-Bis-(N-carbazolyl)-biphenyl),mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, SimCP([3,5-Di(9H-carbazol-9-yl)phenyl]triphenylsilane), Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO(bis[2-(diphenylphosphino)phenyl] ether oxide),9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and/or TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine). The hostmaterial H typically should be selected to exhibit first triplet (T1)and first singlet (S1) energy levels, which are energetically higherthan the first triplet (T1) and first singlet (S1) energy levels of theorganic molecule.

In one embodiment of the invention, the EML comprises a so-calledmixed-host system with at least one hole-dominant host and oneelectron-dominant host. In a particular embodiment, the EML comprisesexactly one light emitting molecule according to the invention E and amixed-host system comprising T2T as electron-dominant host and a hostselected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as hole-dominanthost. In a further embodiment the EML comprises 50-80% by weight,preferably 60-75% by weight of a host selected from CBP, mCP, mCBP,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole,9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole,9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45% by weight,preferably 15-30% by weight of T2T and 5-40% by weight, preferably10-30% by weight of light emitting molecule according to the invention.

Adjacent to the light-emitting layer EML an electron transport layer(ETL) may be located. Herein, any electron transporter may be used.Exemplarily, electron-poor compounds such as, e.g., benzimidazoles,pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole),phosphinoxides and sulfone, may be used. An electron transporter mayalso be a star-shaped heterocycle such as1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL maycomprise NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq₃(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2(2,7-di(2,2′-bipyridin-5-yl)triphenyle), Sif87(dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88(dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB(1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene) and/or BTB(4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl). Optionally,the ETL may be doped with materials such as Liq. The electron transportlayer (ETL) may also block holes or a holeblocking layer (HBL) isintroduced.

The HBL may exemplarily comprise BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=Bathocuproine), BAlq(bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen(2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq₃(Aluminum-tris(8-hydroxyquinoline)), TSPO1(diphenyl-4-triphenylsilylphenyl-phosphinoxide), T2T(2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T(2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST(2,4,6-tris(9,9′-spirobifluorene-2-yl)-1,3,5-triazine), and/or TCB/TCP(1,3,5-tris(N-carbazolyl)benzol/1,3,5-tris(carbazol)-9-yl) benzene).

Adjacent to the electron transport layer (ETL), a cathode layer C may belocated. Exemplarily, the cathode layer C may comprise or may consist ofa metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In,W, or Pd) or a metal alloy. For practical reasons, the cathode layer mayalso consist of (essentially) non-transparent metals such as Mg, Ca orAl. Alternatively or additionally, the cathode layer C may also comprisegraphite and or carbon nanotubes (CNTs). Alternatively, the cathodelayer C may also consist of nanoscalic silver wires.

An OLED may further, optionally, comprise a protection layer between theelectron transport layer (ETL) and the cathode layer C (which may bedesignated as electron injection layer (EIL)). This layer may compriselithium fluoride, cesium fluoride, silver, Liq(8-hydroxyquinolinolatolithium), Li₂O, BaF₂, MgO and/or NaF.

Optionally, also the electron transport layer (ETL) and/or a holeblocking layer (HBL) may comprise one or more host compounds H.

In order to modify the emission spectrum and/or the absorption spectrumof the light-emitting layer EML further, the light-emitting layer EMLmay further comprise one or more further emitter molecules F. Such anemitter molecule F may be any emitter molecule known in the art.Preferably such an emitter molecule F is a molecule with a structurediffering from the structure of the molecules according to the inventionE. The emitter molecule F may optionally be a TADF emitter.Alternatively, the emitter molecule F may optionally be a fluorescentand/or phosphorescent emitter molecule which is able to shift theemission spectrum and/or the absorption spectrum of the light-emittinglayer EML. Exemplarily, the triplet and/or singlet excitons may betransferred from the emitter molecule according to the invention E tothe emitter molecule F before relaxing to the ground state S0 byemitting light typically red-shifted in comparison to the light emittedby emitter molecule E. Optionally, the emitter molecule F may alsoprovoke two-photon effects (i.e., the absorption of two photons of halfthe energy of the absorption maximum).

Optionally, an organic electroluminescent device (e.g., an OLED) mayexemplarily be an essentially white organic electroluminescent device.Exemplarily such white organic electroluminescent device may comprise atleast one (deep) blue emitter molecule and one or more emitter moleculesemitting green and/or red light. Then, there may also optionally beenergy transmittance between two or more molecules as described above.

As used herein, if not defined more specifically in the particularcontext, the designation of the colors of emitted and/or absorbed lightis as follows:

violet: wavelength range of >380-420 nm;

deep blue: wavelength range of >420-480 nm;

sky blue: wavelength range of >480-500 nm;

green: wavelength range of >500-560 nm;

yellow: wavelength range of >560-580 nm;

orange: wavelength range of >580-620 nm;

red: wavelength range of >620-800 nm.

With respect to emitter molecules, such colors refer to the emissionmaximum. Therefore, exemplarily, a deep blue emitter has an emissionmaximum in the range of from >420 to 480 nm, a sky blue emitter has anemission maximum in the range of from >480 to 500 nm, a green emitterhas an emission maximum in a range of from >500 to 560 nm, a red emitterhas an emission maximum in a range of from >620 to 800 nm.

A deep blue emitter may preferably have an emission maximum of below 480nm, more preferably below 470 nm, even more preferably below 465 nm oreven below 460 nm. It will typically be above 420 nm, preferably above430 nm, more preferably above 440 nm or even above 450 nm.

Accordingly, a further aspect of the present invention relates to anOLED, which exhibits an external quantum efficiency at 1000 cd/m² ofmore than 8%, more preferably of more than 10%, more preferably of morethan 13%, even more preferably of more than 15% or even more than 20%and/or exhibits an emission maximum between 420 nm and 500 nm,preferably between 430 nm and 490 nm, more preferably between 440 nm and480 nm, even more preferably between 450 nm and 470 nm and/or exhibits aLT80 value at 500 cd/m² of more than 100 h, preferably more than 200 h,more preferably more than 400 h, even more preferably more than 750 h oreven more than 1000 h. Accordingly, a further aspect of the presentinvention relates to an OLED, whose emission exhibits a CIEy colorcoordinate of less than 0.45, preferably less than 0.30, more preferablyless than 0.20 or even more preferably less than 0.15 or even less than0.10.

A further aspect of the present invention relates to an OLED, whichemits light at a distinct color point. According to the presentinvention, the OLED emits light with a narrow emission band (small fullwidth at half maximum (FWHM)). In one aspect, the OLED according to theinvention emits light with a FWHM of the main emission peak of less than0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45eV, even more preferably less than 0.43 eV or even less than 0.40 eV.

A further aspect of the present invention relates to an OLED, whichemits light with CIEx and CIEy color coordinates close to the CIEx(═0.131) and CIEy (═0.046) color coordinates of the primary color blue(CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020(Rec. 2020) and thus is suited for the use in Ultra High Definition(UHD) displays, e.g. UHD-TVs. Accordingly, a further aspect of thepresent invention relates to an OLED, whose emission exhibits a CIExcolor coordinate of between 0.02 and 0.30, preferably between 0.03 and0.25, more preferably between 0.05 and 0.20 or even more preferablybetween 0.08 and 0.18 or even between 0.10 and 0.15 and/or a a CIEycolor coordinate of between 0.00 and 0.45, preferably between 0.01 and0.30, more preferably between 0.02 and 0.20 or even more preferablybetween 0.03 and 0.15 or even between 0.04 and 0.10.

In a further aspect, the invention relates to a method for producing anoptoelectronic component. In this case an organic molecule of theinvention is used.

The organic electroluminescent device, in particular the OLED accordingto the present invention can be produced by any means of vapordeposition and/or liquid processing. Accordingly, at least one layer is

-   -   prepared by means of a sublimation process,    -   prepared by means of an organic vapor phase deposition process,    -   prepared by means of a carrier gas sublimation process,    -   solution processed or printed.

The methods used to produce the organic electroluminescent device, inparticular the OLED according to the present invention are known in theart. The different layers are individually and successively deposited ona suitable substrate by means of subsequent deposition processes. Theindividual layers may be deposited using the same or differingdeposition methods.

Vapor deposition processes comprise, for example, thermal(co)evaporation, chemical vapor deposition and physical vapordeposition. For active matrix OLED display, an AMOLED backplane is usedas substrate. The individual layer may be processed from solutions ordispersions employing adequate solvents. Solution deposition processexemplarily comprise spin coating, dip coating and jet printing. Liquidprocessing may optionally be carried out in an inert atmosphere (e.g.,in a nitrogen atmosphere) and the solvent may optionally be completelyor partially removed by means known in the state of the art.

EXAMPLES

General Procedure for Synthesis AAV1:

4-bromo-3-fluorobenzotrifluoride (1.0 equivalent),2-fluoro-5-cyanophenylboronic ester (1.2 equivalents), Pd(PPh₃)₄(0.02equivalents), and potassium phosphate (2.50 equivalents) are stirredunder nitrogen atmosphere in a dioxane/water mixture (ratio of 10:1) at100° C. for 22 h. Active carbon and Celite® are added to the reactionmixture and stirred at 90° C. for 10 min, then the mixture is hotfiltered and the organic phase is concentrated under reduced pressure.The residue is purified by chromatography and the product Z1 is obtainedas a solid.

General Procedure for Synthesis AAV2:

3-bromo-4-fluorobenzotrifluoride (1.0 equivalent),2-fluoro-4-cyanophenylboronic ester (1.1 equivalents), Pd(dba)₃C₂(0.04equivalents), SPhos (0.16 equivalents) and potassium phosphate (2.50equivalents) are stirred under nitrogen atmosphere in a dioxane/watermixture (ratio of 10:1) at 100° C. for 22 h. Active carbon and Celite®are added to the reaction mixture and stirred at 90° C. for 10 min, thenthe mixture is hot filtered and the organic phase is concentrated underreduced pressure. The residue is purified by chromatography and theproduct Z2 is obtained as a solid.

General Procedure for Synthesis AAV3:

Z1 or Z2 (1 equivalent each), the corresponding donor molecule D-H (2.00equivalents) and tribasic potassium phosphate (5.0 equivalents) aresuspended under nitrogen atmosphere in DMSO and stirred at 110° C. for23 h. The reaction mixture is poured into a saturated sodium chloridesolution and the resulting precipitate is filtered. Subsequently theresidue is dissolved in dichloromethane and washed with saturated sodiumchloride solution, dried over MgSO₄ and the solvent evaporated underreduced pressure. The crude product is purified by chromatography.

In particular, the donor molecule D-H is a 3,6-substituted carbazole(e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole,3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g.,2,7-dimethylcarbazole, 2,7-diphenylcarbazole,2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g.,1,8-dimethylcarbazole, 1,8-diphenylcarbazole,1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g.,1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole,2-tert-butylcarbazole), or a 3-substituted carbazole (e.g.,3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

Exemplarily a halogen-substituted carbazole, particularly3-bromocarbazole, can be used as D-H. In a subsequent reaction a boronicacid ester functional group or boronic acid functional group may beexemplarily introduced at the position of the one or more halogensubstituents, which was introduced via D-H, to yield the correspondingcarbazol-3-ylboronic acid ester or carbazol-3-ylboronic acid, e.g., viathe reaction with bis(pinacolato)diboron (CAS No. 73183-34-3).Subsequently, one or more substituents R^(a) may be introduced in placeof the boronic acid ester group or the boronic acid group via a couplingreaction with the corresponding halogenated reactant R^(a)-Hal,preferably R^(a)—Cl and R^(a)—Br.

Alternatively, one or more substituents R^(a) may be introduced at theposition of the one or more halogen substituents, which was introducedvia D-H, via the reaction with a boronic acid of the substituent R^(a)[R^(a)—B(OH)₂] or a corresponding boronic acid ester.

In particular, the synthesis of an organic molecule according to theinvention can be performed according to the General synthesis scheme Iwith the synthesis conditions provided by the General procedure forsynthesis AAV1, AAV2, and AAV3, wherein

E0-1 is a bromo-fluoro-substituted trifluorobenzoztrifluoride selectedfrom the group consisting of 4-bromo-3-fluorobenzotrifluoride,3-bromo-4-fluorobenzotrifluoride, 3-bromo-2-fluorobenzotrifluoride,2-bromo-3-fluorobenzotrifluoride; and

E0-2 is a fluoro-cynaophenylboronic ester selected from the groupconsisting of 2-fluoro-5-cyanophenylboronic ester,2-fluoro-4-cyanophenylboronic ester, 2-fluoro-3-cyanophenylboronicester, 2-fluoro-6-cyanophenylboronic ester.

Cyclic Voltammetry

Cyclic voltammograms are measured from solutions having concentration of10⁻³ mol/L of the organic molecules in dichloromethane or a suitablesolvent and a suitable supporting electrolyte (e.g. 0.1 mol/L oftetrabutylammonium hexafluorophosphate). The measurements are conductedat room temperature under nitrogen atmosphere with a three-electrodeassembly (Working and counter electrodes: Pt wire, reference electrode:Pt wire) and calibrated using FeCp₂/FeCp₂ ⁺ as internal standard. TheHOMO data was corrected using ferrocene as internal standard against astandard calomel electrode (SCE).

Density Functional Theory Calculation

Molecular structures are optimized employing the BP86 functional and theresolution of identity approach (RI). Excitation energies are calculatedusing the (BP86) optimized structures employing Time-Dependent DFT(TD-DFT) methods. Orbital and excited state energies are calculated withthe B3LYP functional. Def2-SVP basis sets (and a m4-grid for numericalintegration are used. The Turbomole program package is used for allcalculations.

Photophysical Measurements

Sample pretreatment: Spin-coating

Apparatus: Spin150, SPS euro.

The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 sat 4000 U/min at 1000 Upm/s. After coating, the films are tried at 70°C. for 1 min.

Photoluminescence Spectroscopy and TCSPC (Time-Correlated Single-PhotonCounting)

Steady-state emission spectroscopy is measured by a Horiba Scientific,Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- andemissions monochromators and a Hamamatsu R928 photomultiplier and atime-correlated single-photon counting option. Emissions and excitationspectra are corrected using standard correction fits.

Excited state lifetimes are determined employing the same system usingthe TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

Excitation sources:

NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

SpectraLED 310 (wavelength: 314 nm)

SpectraLED 355 (wavelength: 355 nm).

Data analysis (exponential fit) is done using the software suiteDataStation and DAS6 analysis software. The fit is specified using thechi-squared-test.

Photoluminescence Quantum Yield Measurements

For photoluminescence quantum yield (PLQY) measurements an Absolute PLQuantum Yield Measurement C9920-03G system (Hamamatsu Photonics) isused. Quantum yields and CIE coordinates are determined using thesoftware U6039-05 version 3.6.0.

Emission maxima are given in nm, quantum yields Q0 in % and CIEcoordinates as x,y values. PLQY is determined using the followingprotocol:

-   -   1) Quality assurance: Anthracene in ethanol (known        concentration) is used as reference    -   2) Excitation wavelength: the absorption maximum of the organic        molecule is determined and the molecule is excited using this        wavelength    -   3) Measurement        -   Quantum yields are measured for sample of solutions or films            under nitrogen atmosphere. The yield is calculated using the            equation:

$\Phi_{PL} = {\frac{n_{photon},{emitted}}{n_{photon},{absorbed}} = \frac{\int{{\frac{\lambda}{hc}\left\lbrack {{{Int}_{emitted}^{sample}(\lambda)} - {{Int}_{absorbed}^{sample}(\lambda)}} \right\rbrack}d\; \lambda}}{\int{{\frac{\lambda}{hc}\left\lbrack {{{Int}_{emitted}^{reference}(\lambda)} - {{Int}_{absorbed}^{reference}(\lambda)}} \right\rbrack}d\; \lambda}}}$

-   -   -   wherein n_(photon) denotes the photon count and Int. the            intensity.

Production and Characterization of Organic Electroluminescence Devices

OLED devices comprising organic molecules according to the invention canbe produced via vacuum-deposition methods. If a layer contains more thanone compound, the weight-percentage of one or more compounds is given in%. The total weight-percentage values amount to 100%, thus if a value isnot given, the fraction of this compound equals to the differencebetween the given values and 100%.

The not fully optimized OLEDs are characterized using standard methodsand measuring electroluminescence spectra, the external quantumefficiency (in %) in dependency on the intensity, calculated using thelight detected by the photodiode, and the current. The OLED devicelifetime is extracted from the change of the luminance during operationat constant current density. The LT50 value corresponds to the time,where the measured luminance decreased to 50% of the initial luminance,analogously LT80 corresponds to the time point, at which the measuredluminance decreased to 80% of the initial luminance, LT 95 to the timepoint, at which the measured luminance decreased to 95% of the initialluminance etc.

Accelerated lifetime measurements are performed (e.g. applying increasedcurrent densities). Exemplarily LT80 values at 500 cd/m² are determinedusing the following equation:

${{LT}\; 80\left( {500\; \frac{c\; d^{2}}{m^{2}}} \right)} = {{LT}\; 80\left( L_{0} \right)\left( \frac{L_{0}}{500\; \frac{c\; d^{2}}{m^{2}}} \right)^{1.6}}$

wherein L₀ denotes the initial luminance at the applied current density.

The values correspond to the average of several pixels (typically two toeight), the standard deviation between these pixels is given.

HPLC-MS:

HPLC-MS spectroscopy is performed on a HPLC by Agilent (1100 series)with MS-detector (Thermo LTQ XL). A reverse phase column 4.6 mm×150 mm,particle size 5.0 μm from Waters (without pre-column) is used in theHPLC. The HPLC-MS measurements are performed at room temperature (rt)with the solvents acetonitrile, water and THF in the followingconcentrations:

solvent A: H₂O (90%) MeCN (10%) solvent B: H₂O (10%) MeCN (90%) solventC: THF (100%)

From a solution with a concentration of 0.5 mg/ml an injection volume of15 μL is taken for the measurements. The following gradient is used:

Flow rate [ml/min] time [min] A[%] B[%] D[%] 3 0 40 50 10 3 10 10 15 753 16 10 15 75 3 16.01 40 50 10 3 20 40 50 10

Ionisation of the probe is performed by APCI (atmospheric pressurechemical ionization).

Example 1

Example 1 was synthesized according to AAV1 (yield 16%) and AAV3 (yield71%).

FIG. 1 depicts the emission spectrum of example 1 (10% by weight inPMMA). The emission maximum (λ_(max)) is at 451 nm. Thephotoluminescence quantum yield (PLQY) is 54%, the full width at halfmaximum (FWHM) is 0.40 eV and the emission lifetime is 76 ρs. Theresulting CIE_(x) coordinate is determined at 0.15 and the CIE_(y)coordinate at 0.12.

Example 2

Example 2 was synthesized according to AAV2 (yield 62%) and AAV3 (yield37%).

FIG. 2 depicts the emission spectrum of example 2 (10% by weight inPMMA). The emission maximum (Δ_(max)) is at 467 nm. Thephotoluminescence quantum yield (PLQY) is 67%, the full width at halfmaximum (FWHM) is 0.40 eV and the emission lifetime is 37 μs. Theresulting CIEx coordinate is determined at 0.16 and the CIE_(y)coordinate at 0.20.

Additional Examples of Organic Molecules of the Invention

Although illustrative embodiments of the present invention have beendescribed herein with reference to the accompanying drawings, it is tobe understood that the invention is not limited to those preciseembodiments, and that various other changes and modifications may bemade by one skilled in the art without departing from the scope orspirit of the invention.

1. An organic molecule comprising a structure of Formula I,

wherein T is selected from the group consisting of CN and CF₃; V, W andY is independently from each other selected from the group consisting ofCN, CF₃ and R²; Z is at each occurrence independently from anotherselected from the group consisting of a direct bond, CR³R⁴, C═CR³R⁴,C═O, C═NR³, NR³, O, SiR³R⁴, S, S(O) and S(O)₂; R¹ is at each occurrenceindependently from another selected from the group consisting ofhydrogen, deuterium, C₁-C₅-alkyl, wherein one or more hydrogen atoms areoptionally substituted by deuterium; C₂-C₈-alkenyl, wherein one or morehydrogen atoms are optionally substituted by deuterium; C₂-C₈-alkynyl,wherein one or more hydrogen atoms are optionally substituted bydeuterium; and C₆-C₁₈-aryl, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu and Ph; R² is at each occurrenceindependently from another selected from the group consisting ofhydrogen, deuterium, C₁-C₅-alkyl, wherein one or more hydrogen atoms areoptionally substituted by deuterium; C₂-C₈-alkenyl, wherein one or morehydrogen atoms are optionally substituted by deuterium; C₂-C₅-alkynyl,wherein one or more hydrogen atoms are optionally substituted bydeuterium; and C₆-C₁₈-aryl, which is optionally substituted with one ormore substituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu and Ph; R^(a), R³ and R⁴ is at eachoccurrence independently from another selected from the group consistingof: hydrogen, deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR)₂, OSO₂R⁵, CF₃, CN,F, Br, I, C₁-C₄₀-alkyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₁-C₄₀-alkoxy,which is optionally substituted with one or more substituents R⁵ andwherein one or more non-adjacent CH₂-groups are optionally substitutedby R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R^(S))₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵,P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₁-C₄₀-thioalkoxy, which isoptionally substituted with one or more substituents R⁵ and wherein oneor more non-adjacent CH₂-groups are optionally substituted by R⁵C═CR⁵,C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO,SO₂, NR⁵, O, S or CONR⁵; C₂-C₄₀-alkenyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; R⁵ is at each occurrence independently from anotherselected from the group consisting of hydrogen, deuterium, N(R⁶)₂, OR⁶,Si(Rt)₃, B(OR)₂, OSO₂R⁶, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which isoptionally substituted with one or more substituents R⁶ and wherein oneor more non-adjacent CH₂-groups are optionally substituted by R⁶C═CR⁶,C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO,SO₂, NR⁶, O, S or CONR⁶; C₁-C₄₀-alkoxy, which is optionally substitutedwith one or more substituents R⁶ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂,Sn(R⁶)₂, C═O, C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁶ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁶C═CR⁶, C≡C, Si(R⁶)₂, Ge(R⁶)₂, Sn(R⁶)₂, C═O,C═S, C═Se, C═NR⁶, P(═O)(R⁶), SO, SO₂, NR⁶, O, S or CONR⁶; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁶; andC₃-C₅₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁶; R⁶ is at each occurrence independently from anotherselected from the group consisting of: hydrogen, deuterium, OPh, CF₃,CN, F, C₁-C₅-alkyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₁-C₅-alkoxy, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₁-C₅-thioalkoxy, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₂-C₅-alkenyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₂-C₅-alkynyl, wherein one or more hydrogen atoms are optionally,independently from each other substituted by deuterium, CN, CF₃, or F;C₆-C₁₈-aryl, which is optionally substituted with one or moreC₁-C₅-alkyl substituents; C₃-C₁₇-heteroaryl, which is optionallysubstituted with one or more C₁-C₅-alkyl substituents; N(C₆-C₁₈-aryl)₂;N(C₃-C₁₇-heteroaryl)₂, and N(C₃-C₁₇-heteroaryl)(C₆—C is-aryl); whereinexactly one substituent selected from the group consisting of T, V, Wand Y is CN; and exactly one substituent selected from the groupconsisting of T, V, W and Y is CF₃.
 2. The organic molecule according toclaim 1, wherein the molecule comprises a structure of Formula Ia:

wherein W^(#) is selected from the group consisting of CN and CF₃, andwherein Z, T, R¹, R² and R^(a) have the aforestated meanings, whereinexactly one substituent selected from the group consisting of T andW^(#) is CN; and exactly one substituent selected from the groupconsisting of T and W^(#) is CF₃.
 3. The organic molecule according toclaim 1, wherein the molecule comprises a structure of Formula IIa:

wherein W^(#) is selected from the group consisting of CN and CF₃, andwherein T, R¹, R² and R^(a) have the aforestated meanings, whereinexactly one substituent selected from the group consisting of T andW^(#) is CN; and exactly one substituent selected from the groupconsisting of T, W^(#) is CF₃.
 4. The organic molecule according toclaim 1, wherein R¹ and R² at each occurrence independently from anotherselected from the group consisting of H, methyl, mesityl, tolyl andphenyl.
 5. The organic molecule according to claim 1, wherein R¹ and R²are both H.
 6. The organic molecule according to claim 1, wherein themolecule comprises a structure of Formula IIb:

wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of: deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵),OSO₂R⁵, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-alkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R^(S))₂,C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵; C₆-C₆₀-aryl,which is optionally substituted with one or more substituents R⁵; andC₃-C₇-heteroaryl, which is optionally substituted with one or moresubstituents R⁵; and wherein T, Y W, V, R¹ and R² have the aforestatedmeanings.
 7. The organic molecule according to claim 1, wherein themolecule comprises a structure of Formula IIc:

wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of deuterium, N(R⁵)₂, OR⁵, Si(R⁵)₃, B(OR⁵)₂,OSO₂R⁵, CF₃, CN, F, Br, I, C₁-C₄₀-alkyl, which is optionally substitutedwith one or more substituents R⁵ and wherein one or more non-adjacentCH₂-groups are optionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂,Sn(R⁵)₂, C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-alkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₁-C₄₀-thioalkoxy, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkenyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R⁵)₂, C═O,C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₂-C₄₀-alkynyl, which is optionally substituted with one or moresubstituents R⁵ and wherein one or more non-adjacent CH₂-groups areoptionally substituted by R⁵C═CR⁵, C≡C, Si(R⁵)₂, Ge(R⁵)₂, Sn(R^(S))₂,C═O, C═S, C═Se, C═NR⁵, P(═O)(R⁵), SO, SO₂, NR⁵, O, S or CONR⁵;C₆-C₆₀-aryl, which is optionally substituted with one or moresubstituents R⁵; and C₃-C₅₇-heteroaryl, which is optionally substitutedwith one or more substituents R⁵; and wherein T, Y W, V, R¹ and R² havethe aforestated meanings.
 8. The organic molecule according to claim 6,wherein R^(b) is at each occurrence independently from another selectedfrom the group consisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃, Ph, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; pyridinyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; pyrimidinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃ and Ph; carbazolyl, which is optionally substituted with one or moresubstituents independently from each other selected from the groupconsisting of Me, ^(i)Pr, ^(t)Bu, CN, CF₃ and Ph; triazinyl, which isoptionally substituted with one or more substituents independently fromeach other selected from the group consisting of Me, ^(i)Pr, ^(t)Bu, CN,CF₃, and Ph; and N(Ph)₂. 9.-15. (canceled)
 16. A composition comprising:(a) at least one organic molecule according to claim 1 as an emitterand/or host; (b) one or more emitter and/or host materials differentfrom the at least one organic molecule according to claim 1, and (c)optionally one or more dyes and/or one or more solvents.
 17. Anoptoelectronic device comprising an organic molecule according toclaim
 1. 18. The optoelectronic device according to claim 17, whereinthe optoelectronic device is an organic light-emitting diode,light-emitting electrochemical cell, organic light-emitting sensor, anorganic diode, an organic solar cell, an organic transistor, an organicfield-effect transistor, an organic laser or a down-conversion element.19. The optoelectronic device according to claim 17, wherein the organicmolecule is one of an emitter and an absorber in the optoelectronicdevice.
 20. The optoelectronic device according to claim 16, comprisinga substrate, an anode and a cathode, wherein the anode or the cathode isapplied to the substrate, and at least one light-emitting layer isdisposed between anode and cathode and which comprises the organicmolecule.
 21. An optoelectronic device comprising an organic moleculeaccording to claim
 2. 22. The optoelectronic device according to claim21, wherein the organic molecule is one of an emitter and an absorber inthe optoelectronic component.
 23. An optoelectronic device comprisingthe composition according to claim
 16. 24. The optoelectronic deviceaccording to claim 23, comprising: a substrate, an anode and a cathode,wherein the anode or the cathode are disposed on the substrate, and atleast one light-emitting layer, which is disposed between the anode andthe cathode and which comprises the composition.
 25. The optoelectronicdevice according to claim 23, wherein the composition is one of anemitter and an absorber in the optoelectronic device.
 26. A method forproducing an optoelectronic device, comprising processing of the organicmolecule according to claim 1 by a vacuum process evaporation or from asolution.
 27. A method for producing an optoelectronic device,comprising processing of the composition according to claim 16 by avacuum evaporation process or from a solution.